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Triethylamine → 6-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile

HRID 392370
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HRID 392370 반응식
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5](Cl)=[CH:6][N:7]=1.[F-:11].[K+].[CH3:13][CH:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C(N(CC)CC)C>CS(C)=O.O.C(OCC)(=O)C>[F:11][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:19][C:18]2[CH2:17][CH2:16][C:15](=[O:20])[C:14]=2[CH3:13])=[N:7][CH:6]=1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 130052-Methyl-1,3-cyclopentanedioneHCID 522689Potassium FluorideHCID 226628453,6-Dichloropyrazine-2-carbonitrile

생성물 1

HCID 226628306-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile수율 42.3%

시약·촉매·용매 3

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

In 60 mL of dimethyl sulfoxide was dissolved 3.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 3.0 g of potassium fluoride, the mixture thus obtained was stirred at 90-100° C. for 2 hours. The reaction mixture was returned to room temperature, to which were successively added 2.1 g of 2-methyl-1,3-cyclopentandione and 7.2 ml of triethylamine. The mixture thus obtained was stirred at room temperature for one hour. The reaction mixture was added to a mixture of 50 mL of ethyl acetate and 200 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1] to obtain 1.7 g of 6-fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile as a yellow-colored solid product.

후처리

  1. customthe mixture thus obtained
  2. customwas returned to room temperature, to which
  3. customThe mixture thus obtained
  4. stirringwas stirred at room temperature for one hour
  5. customthe organic layer was separated
  6. customThe organic layer thus obtained
  7. washwas washed successively with water and saturated aqueous solution of sodium chloride
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1]

출처 및 근거

ORD 기록
ord-784edebb176347d0ab6c64e54abfb226
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06800629B2

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